239. Tech Tools: How Smarter Scheduling Leads to Stronger Communication

Summary

Episode Summary: Think Fast Talk Smart, Episode 239

Title: Tech Tools: How Smarter Scheduling Leads to Stronger Communication
Host: Matt Abrahams
Guest: Darren, Calendly Representative
Date: October 30, 2025

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Overview

In this episode of the "Tech Tools" miniseries, Matt Abrahams explores how modern scheduling tools like Calendly do much more than just book meetings—they can fundamentally improve communication workflows, make meetings more purposeful, and drive business success. Darren from Calendly joins to discuss the evolution of smart scheduling tech, new data insights about meetings, the importance of redefining meeting culture, and practical tips for effective workplace communication.

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Key Discussion Points & Insights

1. Calendly's Mission and Expanded Vision

• Pitch Structure (01:12–02:47):
  Matt prompts Darren to describe Calendly using his MBA pitch style: “What if you... so that... For example... And that’s not all.”
  • Darren:
    • Calendly aims to eliminate scheduling back-and-forth, helping users book meetings fast—even routing to the right person or handling payments and group scheduling.
    • The vision now extends beyond just arranging meetings: “What if you could have one platform that... also helps you prepare, engage and follow up on meetings? We've got some advanced AI solutions coming that allow you to address preparation, engagement and follow ups as well." (02:16)
    • Focus is on supporting the full meeting lifecycle for better preparedness, engagement, and follow-up.

2. Origin of Calendly

• Founder's Story (03:02–04:44):
  • CEO Tope Awatona’s background in sales highlighted the pain of endless scheduling emails (“7.6 emails on average” to set a meeting).
  • The desire to keep up momentum and avoid calendar ping-pong led to Calendly’s creation.
  • “It was hurting his pipeline as working in software sales... So he founded Calendly to build that scheduling link that would now become a household name.” (03:21)
  • Calendly evolved to support group scheduling, payment integration, and team distribution for various business needs.

3. Meeting Trends and Surprising Research

• State of Meetings Report 2024 (04:45–06:33):
  • Contrary to the memes about unproductive meetings, data reveals professionals crave more meetings—if they are productive.
  • Key stats:
    • "81% of respondents in this particular study said that more productive meetings... would hopefully work." (05:41)
    • "54% said more meetings would enhance the productivity at work." (05:48)
  • Highlights the contrast between popular perception (“meetings that should have been emails”) and the actual desire for valuable, purposeful interaction.

4. What Makes an Effective Meeting?

• Purpose-Driven Meetings (06:59–07:30):
  • Meetings are essential for decisions, alignment, and action—not just sharing information.
  • “41% of respondents said the external meetings, they're much more productive when they use [them] for direction and goal setting.” (07:10)
  • “If it's for the right reasons, we all crave it... If it's not for the right reasons, if we're just sharing information... we don't want to see it. That competes with productive work.” (07:22)

5. Communication Heroes and Hacks

• Darren’s Communication Inspirations (09:02–09:31):

  • Admires Brian Chesky, CEO of Airbnb, for storytelling ability: “The storyteller archetype, in my view, are the best communicators out there.”
  • Recommends Chesky’s “Airbnb Trips” launch as a prime example: “The way he tells this story for a prolonged period of time had me on the edge of my seat.” (09:13)
  • Storytelling makes complex concepts engaging and memorable—even in meetings.

• Asynchronous Communication (10:00–10:50):

  • Darren champions asynchronous tools (like Loom) to collaborate across time zones and working styles.
  • “Being able to share content in an asynchronous way...video, audio, notes... is really how my team is so effective.” (10:13)
  • Avoid unnecessary meetings: “We all know that often we feel the temptation to just schedule meetings when it’s unnecessary.” (10:06)
  • Use meetings for true collaboration, decision making, and creative iteration.

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Notable Quotes & Moments

• On the purpose of meetings:
  • “The reality is that meetings are where we make money. Meetings are where we align teams, meetings are where we get work done.” — Darren (05:13)
• On storytelling in communication:
  • “Storytelling is a critical skill for getting lots of information across and talk about a tool for engagement. Storytelling actually works...you can bring story into meetings and...make meetings more memorable.” — Matt (09:31)
• On making meetings meaningful:
  • “Make meetings useful instead of competition for getting work done.” — Matt (07:30)
• On asynchronous collaboration:
  • “Asynchronous communication or asynchronous collaboration is how I'm successful... it's a very strong principle in the way I work.” — Darren (10:04, 10:30)

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Timestamps for Important Segments

• 01:12: How Calendly reframes scheduling and the meeting lifecycle
• 03:02: Calendly’s origin story and initial vision
• 04:45: Meeting research results—why professionals want more (not less) meetings
• 06:59: What separates a productive meeting from a waste of time
• 09:02: Communication role models and the power of storytelling
• 10:00: Asynchronous tools and strategies for effective team collaboration

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Conclusion

Matt and Darren’s conversation dives deep into the evolving mindset around meetings and how the right technological tools—when combined with communication best practices—elevate both productivity and human connection at work. Whether it's leveraging automated scheduling, focusing meetings on decision-making, or embracing storytelling and asynchronous channels, the episode offers practical insights that any leader or team can use to communicate smarter and more effectively.

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Listen to this episode for actionable takeaways on meeting innovation, communication hacks, and leadership storytelling—all from industry experts dedicated to making work life more impactful and efficient.

Transcript

[A]

This Tech Tools miniseries is brought to you by Prezi, the presentation tool that makes your ideas easy to follow, hard to forget, and faster than ever to create. With Prezi AI, the best investment is in the tools of one's own trade. At Think Fast, Talk Smart, we're taking this quote by Benjamin Franklin, the famous US Inventor and founding father, very seriously. As you know, our show strives to share tips and techniques to help you hone and and improve your communication and careers. These practices and approaches can be augmented with tools and technology. I'm Matt Abrahams. I teach Strategic Communication at Stanford Graduate School of Business. Welcome to this Tech Tools miniseries of Think Fast Talk Smart, the podcast. In this multi part miniseries, we'll introduce you to tools we use at Think Fast Talk Smart to help us be better at our spoken and written communication. And you'll learn best practices from the founders who created them. Taken together, we hope these communication tools will help you find new ways to think fast and talk smart.

[B]

Hi Darren, welcome. I'm really excited to have you on the show.

[C]

Likewise. Thanks Matt. Really excited to be here.

[B]

So many of us have likely scheduled a meeting through Calendly, but some of our listeners might not know exactly what Calendly is. Can you share what your product is using the pitch structure I teach my MBA students, which is what if you so that for example, and that's not all.

[C]

What if you could avoid the back and forth of scheduling, the sharing, availability, navigating time zones, or even working out who the right person is to meet from your business so that you can schedule faster, get the right person in front of the right team, and ultimately turn those meetings into revenue candidates in the right roles and a much more efficient way to engage with your customers, clients, stakeholders, partners, candidates, whoever it is that you meet to get business done. For example, you can embed Calendly on your website. People can come to you, they can find a time that works for them, they can even pay you depending on the service that you use. Or they may be routed to the right person if they're looking for a demo, get them to the right territory manager or the right person to meet with them. Or you can look across multiple schedules to find the group of people that they need to meet with in many cases. But that's not all. What if you could have one platform that not just allowed the ease of scheduling like you're used to with Calendly today, but it also helps you prepare, engage and follow up on meetings. So we've got some advanced AI solutions coming that allow you to address preparation, engagement and follow ups as well. We all know meeting life cycle is not just about how meetings are scheduled, but how to make the meetings successful before, during and after. So lots to share there soon as well.

[B]

That's really exciting. Just taking out the struggle of scheduling a meeting, but to then add on to it, increasing the likelihood of success. Sounds great. Thank you. So I'm curious to get the origin story of Callan Lee. What led to the creation of the tool?

[C]

Yeah. So our founder and CEO Tope Awatona, who is our CEO today, still in 2013, he was working in a sales role and like many of us who are selling either with a title that looks like a salesperson or just in our everyday professional lives, we all do a lot of selling. He was spending such a large part of his day going backwards and forwards, trying to find the right time and trying to get the right people on the calendar by navigating schedules. And we all know when you're booking a meeting with a prospect, a candidate, a partner, an advisor, whoever it is, you don't lose that momentum. I don't want to have 7.6 emails, which we know on average it takes to get meetings scheduled. If they're interested in meeting me, I want to meet them as quick and as easy and as painlessly as I can. So that frustrated top, it was hurting his pipelines as working in software sales. So he found a calendar to build a solution to build that scheduling link that would now become a household name. So that was 2013 and naturally you add in all the layers from there. It's really great for you and I to be able to schedule seamlessly, but I actually need a more technical resource to join this demo or I want to share the load around amongst the four or five of us that work in a team. Or I want you to be able to book your home services appointment via my website and then actually want to charge you right then and there because that's how I make money as a small business owner. All of these features and use cases allowed us to become the scheduling automation platform that we are today. The next piece of the puzzle is very much the meeting itself. It's an honor to be a part of so many hundreds of millions of meetings a year, but being a part in terms of scheduling is a small piece of the puzzle and we know that our customers are looking to us for more of the life cycle. How do we prepare and engage in follow up on the meetings as well. And that's where we're heading as A business.

[A]

Thanks for that.

[B]

And it's certainly a ripe field. Right? There's a lot that can be done. I know your firm has conducted research into meetings. What are some of the most interesting and useful results that you found from that research?

[C]

We've been talking about meetings for more than 10 years, and it's an area that anyone who, you know, has an interest in productivity in the workplace and the way we work together thinks about a lot, naturally. We've actually just released our State of meetings report for 2024 and it's a really good read. I can, I can pass on a link if you're interested. But what I found fascinating was the change in perspective over time. So we all talk pretty poorly about meetings. There's lots of memes out there about meetings that should have been emails, and we all purport to want less meetings and meetings that didn't need to be meetings and all that sort of sentiment. But the reality is that meetings are where we make money. Meetings are where we align teams, meetings are where we get work done. In many roles, especially customer or externally facing roles, without meetings, you don't make money, you don't get any work done. But the reality is, obviously many meetings are not effective. Many meetings suck. They don't achieve those outcomes. And for the first time in all the years I've been thinking about this, that was really clear in the data where respondents, professionals, the thousands of people we spoke to, really said quite expressly that more meetings would be helpful. They want more meetings. 81% of respondents in this particular study said that more productive meetings or more meetings that were productive would hopefully work. And 54% said more meetings would enhance the productivity at work. So on one sense, on one side, we're out there talking about meetings that should have been emails, these unproductive days that I spend in meetings, but then the overwhelming majority of professionals saying, give me more, I need more meetings. And that's a really interesting dichotomy to reconcile.

[B]

I can certainly appreciate the need for effective meetings, and that's really where it becomes the challenge. And effective could be who's in the room, what we're trying to accomplish. So I'm glad that there's data that are helping us hone in and figure out what is desired out of meetings, because many of our meetings aren't as effective as they could have been. And helping people understand what makes for an effective meeting, I think is really helpful.

[C]

I used to say meetings debate, decision making and discussion. And we saw that, right? 41% of respondents said the external meetings, they're much more productive when they use for direction and goal setting. A similar proportion said when they use for decision making. That's exactly it. It's what's the purpose of the meeting? Why do I need the meeting? If it's for the right reasons, we all crave it. We want more of them. If it's not for the right reasons, if we're just sharing information, if we're going in circles without a clear goal or objective, we don't want to see it. That competes with productive work.

[B]

Absolutely. So make meetings useful instead of competition for getting work done. Thank you for that.

[A]

We'll be right back to finish our conversation, but first we're going to take a quick break for a message from our sponsors. These sponsorships support the cost of making our show, allowing us to bring it to you free of charge. This episode of Think Fast Talk Smart is brought to you by Squarespace, the all in one platform that helps you turn your ideas into a professional online presence. As someone who teaches communication, I always say that how you present yourself matters not just in person, but online too. Whether you're building a personal brand, sharing your research or launching a new project, Squarespace gives you everything you need to.

[D]

Communicate clearly and confidently.

[A]

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[B]

Of the guests of this miniseries two questions.

[A]

Are you ready for this?

[C]

Let's do it.

[D]

All right.

[B]

I'd be very curious who is a communicator you admire and why?

[C]

The storyteller archetype, in my view are the best communicators out there. And I was just thinking then about who I would describe. I'll tell you a storyteller who I really admire. Brian Chesters and CEO of Airbnb. Go and look up the when they announced trips, one of their new features. The way he tells this story for a prolonged period of time had me on the edge of my seat. And I think it's such a great example of the importance of storytelling in everything you do professionally and personally. So big fan of his as a communicator.

[B]

For that reason, I think storytelling is a critical skill for getting lots of information across and talk about a tool for engagement. Storytelling actually works something that many people don't think about. Germane to what we're talking about is you can bring story into meetings and in fact it can help make meetings more memorable. So thank you for highlighting that Final question beyond your tool, beyond calendly, what is one communication hack tool or shortcut that you use to help yourself be more effective in your communication?

[C]

So this might sound strange being in the business of meetings, but asynchronous communication or asynchronous collaboration is how I'm successful. So what I mean by that is I spoke earlier about when you need a meeting and when you don't. But when I don't need a meeting, I still need to collaborate with my peers. And we all know that often we feel the temptation to just schedule meetings when it's unnecessary. So I know you've spoken to the folks at Loom who I'm a big fan of. But as a principal in general, being able to share content in an asynchronous way, video, audio, notes, high bandwidth ways of sharing too, right? Rather than just a message or an email, is really how my team is so effective, particularly across time zones, remote, different working styles and so on. It's a very strong principle in the way I work and I collaborate by using video, audio and the like to share messages asynchronously.

[B]

I really appreciate that because that is a super useful strategy for getting things done and it allows meetings to serve the function that meetings should, which is for creative collaboration. The ability to iterate and decide and challenge it offloads a lot of the things that we use meetings for. One of the most important things I think I really want to highlight that you said is these are for the interactions that allow for the meetings to be effective and I really appreciate that.

[C]

Darren.

[B]

This has been a great conversation. You've given us lots of insights into how we not only can schedule and plan for our meetings, but some of the things that we should be thinking about and doing when we are actually meeting. I appreciate your time and I appreciate the advice.

[C]

Great to chat. Thanks very much for having me.

[A]

Thank you for joining us for one of our communication tools, episodes of Think Fast, Talk Smart, the podcast. Please be sure to listen to all of the episodes in this miniseries. We appreciate Prezi's sponsorship of these episodes. This episode was produced by Kathryn Reed, Ryan Campos and me, Matt Abrahams. Our music is from Floyd Wonder with special thanks to Podium podcast company. Please find us on YouTube and wherever you get your podcasts. Be sure to subscribe and rate us. Follow us on LinkedIn, TikTok and Instagram and check out fastersmarterio for deep dive videos, English language learning content and our newsletter. Please consider our premium offering for extended Deep Thinks episodes, Ask Matt Anythings and much more at fastersmarter IO Premium.

[D]

I wanted to share with you that over the past few months I've had the amazing opportunity of talking to listeners across the globe about the impact the PODC podcast has had on them. I love learning how people are applying the principles and concepts that we cover on the podcast and the impact that it has had on their lives. It is truly inspiring. Speaking on behalf of all of us that bring you the show, we thank you for your support. We look forward to bringing you new episodes, new techniques and deeper knowledge and we ask for your support. It takes time and effort to put this show on the air. Please keep your ideas coming and if you can, we'd love for you to join our premium. Thank you. And here's to another 200 episodes.